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Which of the following compounds is most...

Which of the following compounds is most susceptible to a nucleophilic attack at the carbonyl group?
(a)`CH_(3)COOCH_(3 )`
(b)`CH_(3)CONH_(2 )`
(c)`CH_(3)COOCOCH_(3 )`
(d) `CH_(3)COCl `

A

` CH_(3)COOCH_(3 )`

B

`CH_(3)CONH_(2 )`

C

` CH_(3)COOCOCH_(3 )`

D

` CH_(3)COCl `

Text Solution

AI Generated Solution

The correct Answer is:
To determine which of the given compounds is most susceptible to a nucleophilic attack at the carbonyl group, we need to analyze the electrophilicity of the carbonyl carbon in each compound and the quality of the leaving groups attached. ### Step-by-Step Solution: 1. **Identify the Compounds**: - (a) `CH3COOCH3` (Methyl acetate) - (b) `CH3CONH2` (Acetamide) - (c) `CH3COOCOCH3` (Diethyl carbonate) - (d) `CH3COCl` (Acetyl chloride) 2. **Analyze the Electrophilicity**: - The electrophilicity of the carbonyl carbon is influenced by the presence of electron-donating or electron-withdrawing groups. - Electron-donating groups (like -OCH3 and -NH2) will decrease the electrophilicity of the carbonyl carbon, making it less susceptible to nucleophilic attack. - Electron-withdrawing groups (like -Cl) will increase the electrophilicity of the carbonyl carbon, making it more susceptible to nucleophilic attack. 3. **Evaluate Each Compound**: - **(a) Methyl acetate (`CH3COOCH3`)**: The -OCH3 group donates electron density through resonance, decreasing the electrophilicity of the carbonyl carbon. - **(b) Acetamide (`CH3CONH2`)**: The -NH2 group also donates electron density through resonance, similarly decreasing the electrophilicity of the carbonyl carbon. - **(c) Diethyl carbonate (`CH3COOCOCH3`)**: The presence of two -O groups can lead to some resonance stabilization, which may decrease the electrophilicity of the carbonyl carbon. - **(d) Acetyl chloride (`CH3COCl`)**: The -Cl group is a strong electron-withdrawing group and does not donate electron density. It is also a very good leaving group, which enhances the electrophilicity of the carbonyl carbon. 4. **Conclusion**: - Among the four compounds, acetyl chloride (`CH3COCl`) has the most electrophilic carbonyl carbon due to the presence of the -Cl group, which is a strong electron-withdrawing group and a good leaving group. Therefore, it is the most susceptible to nucleophilic attack. ### Final Answer: The compound most susceptible to a nucleophilic attack at the carbonyl group is **(d) `CH3COCl`**.
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